Identification

Name
Lincomycin
Accession Number
DB01627
Type
Small Molecule
Groups
Approved, Vet approved
Description

An antibiotic produced by Streptomyces lincolnensis var. lincolnensis. It has been used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.

Structure
Thumb
Synonyms
  • LCM
  • Lincomycine
External IDs
U-10,149 / U-10149
Product Ingredients
IngredientUNIICASInChI Key
Lincomycin hydrochlorideGCW8Y9936L859-18-7POUMFISTNHIPTI-BOMBIWCESA-N
Lincomycin hydrochloride monohydrateM6T05Z2B687179-49-9LFZGYTBWUHCAKF-DCNJEFSFSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LincocinCapsule500 mgOralPfizer1964-12-312006-08-02Canada
LincocinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalPharmacia & Upjohn Inc1964-12-29Not applicableUs
LincocinSolution300 mgIntramuscular; IntravenousPfizer1964-12-312016-05-06Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
LincomycinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalX Gen Pharmaceuticals, Inc.2015-07-05Not applicableUs
LincomycinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalX Gen Pharmaceuticals, Inc.2015-07-05Not applicableUs
International/Other Brands
Lincobect / Lincorex
Categories
UNII
BOD072YW0F
CAS number
154-21-2
Weight
Average: 406.54
Monoisotopic: 406.213757997
Chemical Formula
C18H34N2O6S
InChI Key
OJMMVQQUTAEWLP-KIDUDLJLSA-N
InChI
InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
IUPAC Name
(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboximidic acid
SMILES
[H][C@](C)(O)[C@@]([H])(N=C(O)[C@]1([H])C[C@@]([H])(CCC)CN1C)[C@@]1([H])O[C@]([H])(SC)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O

Pharmacology

Indication

Lincomycin is an antibiotic used in the treatment of staphylococcal, streptococcal, and Bacteroides fragilis infections.

Associated Conditions
Pharmacodynamics

Lincomycin is a lincosamide antibiotic that comes from the yeast Streptomyces lincolnensis. Lincomycin has been shown to be active in vitro against the following microorganisms: Aerobic gram-positive cocci: Streptococcus pyogenes and Viridans group streptococci; Aerobic gram-positive bacilli: Corynebacterium diphtheriae; Anaerobic gram-positive non-sporeforming bacilli: Propionibacterium acnes; Anaerobic gram-positive sporeforming bacilli: Clostridium tetani and Clostridium perfringens.

Mechanism of action

Lincomycin inhibits protein synthesis in susceptible bacteria by binding to the 50 S subunits of bacterial ribosomes and preventing peptide bond formation upon transcription. It is usually considered bacteriostatic, but may be bactericidal in high concentrations or when used against highly susceptible organisms.

TargetActionsOrganism
A50S ribosomal protein L10
inhibitor
Shigella flexneri
Absorption

Rapidly absorbed from the gastrointestinal tract following oral administration. Approximately 20 to 30% absorbed orally in fasting state; absorption decreased when taken with food.

Volume of distribution
Not Available
Protein binding

Protein binding decreases with increased plasma concentrations. Range, 28 to 86% (average, 70 to 75%). Albumin is not thought to be the primary binding component.

Metabolism

Presumed hepatic, however metabolites have not been fully characterized.

Route of elimination

Urinary excretion after this dose ranges from 1.8 to 24.8 percent (mean: 3 percent). Tissue level studies indicate that bile is an important route of excretion.

Half life

The biological half-life after intramuscular or intravenous administration is 5.4 ± 1.0 hours. The serum half-life of lincomycin may be prolonged in patients with severe impairment of renal function compared to patients with normal renal function. In patients with abnormal hepatic function, serum half-life may be twofold longer than in patients with normal hepatic function.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategory
Lincomycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Lincomycin.
AlcuroniumLincomycin may increase the neuromuscular blocking activities of Alcuronium.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Lincomycin.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Lincomycin.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Lincomycin.
AlosetronThe risk or severity of adverse effects can be increased when Lincomycin is combined with Alosetron.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Lincomycin.
AmikacinThe risk or severity of adverse effects can be increased when Lincomycin is combined with Amikacin.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Lincomycin.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Lincomycin.
Food Interactions
  • Take on an empty stomach, food decreases absorption.

References

Synthesis Reference

Alexander D. Argoudelis, David W. Stroman, "Process of producing lincomycin nucleotides." U.S. Patent US4464466, issued June, 1972.

US4464466
General References
Not Available
External Links
KEGG Drug
D00223
KEGG Compound
C06812
PubChem Compound
3000540
PubChem Substance
46506668
ChemSpider
2272112
BindingDB
50335522
ChEBI
6472
ChEMBL
CHEMBL1447
Therapeutic Targets Database
DAP000839
PharmGKB
PA164749212
HET
3QB
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Lincomycin
ATC Codes
J01FF02 — Lincomycin
PDB Entries
4wh5 / 5hkv

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableBacterial Infections1
1CompletedNot AvailableHealthy Volunteers1
1CompletedOtherHealthy Male Chinese Volunteers1
1CompletedOtherHealthy Male Volunteers1
1CompletedTreatmentHealthy Volunteers1
2CompletedPreventionMigraines1
2CompletedTreatmentNonconvulsive Seizures1
2Not Yet RecruitingTreatmentGlioma of Brain / Gliomas / Neoplasms, Brain1
3Active Not RecruitingTreatmentEpilepsies1
3CompletedTreatmentEpilepsies1
4Active Not RecruitingTreatmentCellulitis1
4CompletedTreatmentEpilepsy, Localization Related1
Not AvailableCompletedNot AvailableFocal Epilepsy With and Without Secondary Generalization1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Bimeda Inc.
  • Carlisle Laboratories Inc.
  • Clint Pharmaceutical Inc.
  • Dispensing Solutions
  • Keene Pharmaceuticals Inc.
  • Llorens Pharmaceutical
  • Martin Surgical Supply
  • Medisca Inc.
  • Nord Ost Corp.
  • Pharmacia Inc.
  • Preferred Pharmaceuticals Inc.
  • Raz Co. Inc.
Dosage forms
FormRouteStrength
CapsuleOral500 mg
SolutionIntramuscular; Intravenous300 mg
Injection, solutionIntramuscular; Intravenous; Subconjunctival300 mg/1mL
Prices
Unit descriptionCostUnit
Lincocin 300 mg/ml vial7.79USD ml
Lincomycin hcl powder3.29USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.56HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.02 mg/mLALOGPS
logP0.34ALOGPS
logP-2.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)8.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.98 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.19 m3·mol-1ChemAxon
Polarizability43.91 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5937
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7945
P-glycoprotein inhibitor INon-inhibitor0.6755
P-glycoprotein inhibitor IINon-inhibitor0.5633
Renal organic cation transporterNon-inhibitor0.8868
CYP450 2C9 substrateNon-substrate0.8417
CYP450 2D6 substrateNon-substrate0.8837
CYP450 3A4 substrateSubstrate0.6389
CYP450 1A2 substrateNon-inhibitor0.9222
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9269
CYP450 2C19 inhibitorNon-inhibitor0.9203
CYP450 3A4 inhibitorNon-inhibitor0.9342
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.7696
CarcinogenicityNon-carcinogens0.9482
BiodegradationNot ready biodegradable0.9622
Rat acute toxicity2.5777 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9847
hERG inhibition (predictor II)Non-inhibitor0.7163
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.07 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000j-0900000000-1f46f29c3d5dbc6c25f6
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0901000000-3fc103447a71fd95cedd
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-016r-0895000000-4b0507fffd39d9fc075f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00mk-0952000000-ca2f735ea2244e1cb32e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0901200000-cc68fda14967bfcd7357
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-70466cfb7e0692d073a0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-b712dc39bbf605193fb4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0109000000-cdbfa33f16a571dd85ee
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0209000000-8ec5c595eb6720c93c13

Taxonomy

Description
This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Thioglycosides / Pyrrolidinecarboxamides / Monosaccharides / N-alkylpyrrolidines / Oxanes / Monothioacetals / Trialkylamines / Secondary carboxylic acid amides / Secondary alcohols
show 8 more
Substituents
Proline or derivatives / Alpha-amino acid amide / Glycosyl compound / S-glycosyl compound / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Monosaccharide / Oxane / N-alkylpyrrolidine / Monothioacetal
show 23 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid amide, pyrrolidinecarboxamide, L-proline derivative, carbohydrate-containing antibiotic, S-glycosyl compound (CHEBI:6472)

Targets

Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Yes
Actions
Inhibitor
General Function
Structural constituent of ribosome
Specific Function
Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA (By similarity).Forms part of the ribosomal stalk, playing a cent...
Gene Name
rplJ
Uniprot ID
P0A7J6
Uniprot Name
50S ribosomal protein L10
Molecular Weight
17711.38 Da
References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  2. Odom OW, Hardesty B: Use of 50 S-binding antibiotics to characterize the ribosomal site to which peptidyl-tRNA is bound. J Biol Chem. 1992 Sep 25;267(27):19117-22. [PubMed:1527036]
  3. Champney WS, Tober CL: Specific inhibition of 50S ribosomal subunit formation in Staphylococcus aureus cells by 16-membered macrolide, lincosamide, and streptogramin B antibiotics. Curr Microbiol. 2000 Aug;41(2):126-35. [PubMed:10856379]

Drug created on August 29, 2007 15:12 / Updated on October 01, 2018 16:41